Development of variously functionalized nitrile oxides
N-Methylated amides (N,4-dimethylbenzamide and N-methylcyclohexanecarboxamide) were systematically subjected to chemical transformations, namely, N-tosylation followed by nucleophilic substitution. The amide function was converted to the corresponding carboxylic acid, esters, amides, aldehyde, and k...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2015-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.11.138 |
| _version_ | 1818416521599254528 |
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| author | Haruyasu Asahara Keita Arikiyo Nagatoshi Nishiwaki |
| author_facet | Haruyasu Asahara Keita Arikiyo Nagatoshi Nishiwaki |
| author_sort | Haruyasu Asahara |
| collection | DOAJ |
| description | N-Methylated amides (N,4-dimethylbenzamide and N-methylcyclohexanecarboxamide) were systematically subjected to chemical transformations, namely, N-tosylation followed by nucleophilic substitution. The amide function was converted to the corresponding carboxylic acid, esters, amides, aldehyde, and ketone upon treatment with hydroxide, alkoxide, amine, diisobutylaluminium hydride and Grignard reagent, respectively. In these transformations, N-methyl-N-tosylcarboxamides behave like a Weinreb amide. Similarly, N-methyl-5-phenylisoxazole-3-carboxamide was converted into 3-functionalized isoxazole derivatives. Since the amide was prepared by the cycloaddition reaction of ethynylbenzene and N-methylcarbamoylnitrile oxide, the nitrile oxide served as the equivalent of the nitrile oxides bearing a variety of functional groups such as carboxy, alkoxycarbonyl, carbamoyl, acyl and formyl moieties. |
| first_indexed | 2024-12-14T11:52:13Z |
| format | Article |
| id | doaj.art-8850991f4e9140f7b4e09fce657488e4 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T11:52:13Z |
| publishDate | 2015-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-8850991f4e9140f7b4e09fce657488e42022-12-21T23:02:17ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-07-011111241124510.3762/bjoc.11.1381860-5397-11-138Development of variously functionalized nitrile oxidesHaruyasu Asahara0Keita Arikiyo1Nagatoshi Nishiwaki2School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, JapanSchool of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, JapanSchool of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, JapanN-Methylated amides (N,4-dimethylbenzamide and N-methylcyclohexanecarboxamide) were systematically subjected to chemical transformations, namely, N-tosylation followed by nucleophilic substitution. The amide function was converted to the corresponding carboxylic acid, esters, amides, aldehyde, and ketone upon treatment with hydroxide, alkoxide, amine, diisobutylaluminium hydride and Grignard reagent, respectively. In these transformations, N-methyl-N-tosylcarboxamides behave like a Weinreb amide. Similarly, N-methyl-5-phenylisoxazole-3-carboxamide was converted into 3-functionalized isoxazole derivatives. Since the amide was prepared by the cycloaddition reaction of ethynylbenzene and N-methylcarbamoylnitrile oxide, the nitrile oxide served as the equivalent of the nitrile oxides bearing a variety of functional groups such as carboxy, alkoxycarbonyl, carbamoyl, acyl and formyl moieties.https://doi.org/10.3762/bjoc.11.138acylnitrile oxideamideformylnitrile oxidefunctionalized nitrile oxideWeinreb amide |
| spellingShingle | Haruyasu Asahara Keita Arikiyo Nagatoshi Nishiwaki Development of variously functionalized nitrile oxides Beilstein Journal of Organic Chemistry acylnitrile oxide amide formylnitrile oxide functionalized nitrile oxide Weinreb amide |
| title | Development of variously functionalized nitrile oxides |
| title_full | Development of variously functionalized nitrile oxides |
| title_fullStr | Development of variously functionalized nitrile oxides |
| title_full_unstemmed | Development of variously functionalized nitrile oxides |
| title_short | Development of variously functionalized nitrile oxides |
| title_sort | development of variously functionalized nitrile oxides |
| topic | acylnitrile oxide amide formylnitrile oxide functionalized nitrile oxide Weinreb amide |
| url | https://doi.org/10.3762/bjoc.11.138 |
| work_keys_str_mv | AT haruyasuasahara developmentofvariouslyfunctionalizednitrileoxides AT keitaarikiyo developmentofvariouslyfunctionalizednitrileoxides AT nagatoshinishiwaki developmentofvariouslyfunctionalizednitrileoxides |